Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 83766-88-5, 2-(tert-Butoxy)pyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C9H13NO, blongs to pyridine-derivatives compound. Computed Properties of C9H13NO

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83766-88-5, 2-(tert-Butoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 133928-73-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 133928-73-1, name is 2-Chloro-3-methyl-4-pyridinecarboxylic Acid. This compound has unique chemical properties. The synthetic route is as follows.

2-Chloro-3-methyl-4-pyridinecarboxylic acid (30 g; 174 mmol) was dissolved in pyri- dine (250 ml) and cooled to 0 0C. Methanesulfonyl chloride (13.6 ml) was then added dropwise and the reaction mixture was stirred at 0 0C for 1 hour. NH3 (gas) was added under pressure and the reaction mixture was stirred at room temperature for 1 h. After the reaction had reached completion, the excess NH3 was removed in vacuo. The reaction mixture was then cooled to 0 0C, methanesulfonyl chloride (140 ml) was added and the reaction mixture stirred at room temperature overnight. The mixture was then poured into 0.1 M HCl (200 ml ) at 0 0C (with care), and adjusted to pH =7 with 1 M NaOH. The reaction mixture was extracted with EtOAc (2 x 100 ml), washed with brine, dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was purified by flash column chromatography over silica gel (Biotage flash purification system; gradient: EtO Ac/heptane from 15/85 to 30/70). The product fractions were collected and the solvent was evaporated in vacuo. Yield: 12.6 g of Dl.

According to the analysis of related databases, 133928-73-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/135944; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 36404-88-3, name is 2-Chloro-3-formylpyridine, molecular formula is C6H4ClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Computed Properties of C6H4ClNO

Elemental sodium (0.35 g, 15.0 mmol) was added to dry MeOH (6 mL) at 0 C and allowed to dissolve completely. A solution of 2-chloronicotinaldehyde (0.708, 5.0 mmol) in dry MeOH (2 mL) was added via syringe and the reaction was heated at reflux temperature for 5 hours. The reaction mixture was cooled to room temperature and evaporated under reduced pressure. The residue was taken up in water (10 mL), neutralized with dilute HCl and extracted with Et2O (3 × 10 mL). The organic extracts were dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (petroleum ether/EtOAc, 4:1) to give the title compound, 8 (0.473, 69%), as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 10.34 (d, J = 0.8 Hz, 1H), 8.36 (dd, J = 4.9, 2.1 Hz, 1H), 8.09 (dd, J = 7.4, 2.1 Hz, 1H), 7.00 (ddd, J = 7.4, 4.9, 0.8 Hz, 1H), 4.07 (s, 3H). 13C NMR (75 MHz, CDCl3) delta 189.1, 164.4, 152.8, 137.6, 118.8, 117.3, 54.0

With the rapid development of chemical substances, we look forward to future research findings about 36404-88-3.

Reference:
Article; Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Braeuner-Osborne, Hans; Kristensen, Jesper Langgaard; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3933 – 3937;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, molecular weight is 175.108, as common compound, the synthetic route is as follows.SDS of cas: 131747-62-1

A solution of 180 (100 mg, 0.617 mmol) in toluene 15 ml was added 66 (151.2 mg, 0.864 mmol). PTSA (234.5 mg, 1.234 mmol) was added to the reaction mass. The reaction was stirred at 120 C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude 183, used the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131747-62-1, 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; US2015/72980; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73406-50-5, Adding some certain compound to certain chemical reactions, such as: 73406-50-5, name is Ethyl 3-hydroxypicolinate,molecular formula is C8H9NO3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 73406-50-5.

To 3-hydroxypyridine-2-carboxylic acid (25 g, 179.5 mmol) in a 1 L dried flask was added 400 mL ethanol and 100 mL toluene followed by the addition of 10 mL sulfuric acid. The mixture was heated at reflux (95 C.) for 3 days. After cooling to rt, the mixture was concentrated to ¼ of its volume, and diluted with 600 mL ethyl acetate and 200 mL water. The aqueous layer was extracted with 200 mL ethyl acetate, and the combined organic layers were washed with sat NaHCO3 (3×200 mL), brine, and dried over Na2SO4. The solid was filtered off and the solvent was concentrated under reduced pressure to give 21.9 g of ethyl 3-hydroxypyridine-2-carboxylate (73%), which was used in the next step without purification. This ester (21.9 g, 131 mmol) was dissolved in pyridine and cooled to -40 C., followed by addition of trifluoromethanesulfonic anhydride (48 g, 170 mmol). The reaction mixture was then warmed to 0 C. for 30 min, and then warmed to rt for another 30 min. Water (100 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×200 mL), and the combined organic layers were washed with sat sodium bicarbonate (200 mL), water (200 mL), brine (200 mL), and dried over sodium sulfate. The solid was filtered off, and the solvent was removed under reduced pressure to give 39 g (99%) of desired product, which was used in the next step without further purification. 1H NMR (300 MHz, CD2Cl2) delta 8.73 (dd, 1H), 7.72 (dd, 1H), 7.62 (dd, 1H), 4.46 (q, 2H), 1.42 (t, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharmaceuticals Corporation; US2005/192294; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1124-29-4, name is 5-Acetylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Acetylpyridin-2(1H)-one

General procedure: To a solution of 111-3 (1 eq.) in DCM (0.1 mmol/mL) was added boronic acid III-4 (2 eq.), Cu(OAc)2 (1 eq), Pyridine (10 eq.) and Pyridine-N-Oxide (2 eq.), followed by addition of4A molecular sieve (quantity approx. equal to 111-3 ). The reaction mixture was stirred at rt underoxygen atmosphere overnight. After completion of the reaction indicated by TLC, the resultingmixture was filtered and washed with , the filtrate was washed with brine, dried over Na2SO4 andconcentrated. The residue was purified by column chromatography on silica gel to give 111-5.[0316] Compound 10 (61% yield): ?H NMR (DMSO-d6, 400 MHz) (5 8.43 (d, J = 2.4 Hz, 1H), 7.90 (dd, J= 9.6, 2.4 Hz, 1H), 7.39 (d, J= 8.8 Hz, 2H), 7.06 (d, J= 8.8 Hz, 2H), 6.51 (d, J = 9.6 Hz, 1H), 3.81 (s, 3H), 2.41 (s, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1124-29-4, 5-Acetylpyridin-2(1H)-one.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, molecular formula is C6H5BrClN, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of 3-Bromo-2-chloro-4-methylpyridine

(2) Synthesis of 3-bromo-2-methoxy-4-methylpyridine 3-bromo-2-chloro-4-methylpyridine (1 g) was added to DMF (5.6 mL). Sodium methoxide (28% solution in methanol, 4.6 mL) was added to the solution, and the mixture was stirred at 100 C. for 12 hours. The reaction mixture was partitioned by adding ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (1.1 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.40 (s, 3H), 4.00 (s, 3H), 6.77 (d, J=5.1 Hz, 1H), 7.94 (d, Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 55404-31-4.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 56149-30-5, name is 2-Chloro-N-(4-methoxyphenyl)nicotinamide, the common compound, a new synthetic route is introduced below. Formula: C13H11ClN2O2

B. N-(4-Methoxyphenyl)-2-[1-(4-pyridyl)piperidin-4-yl-methyl]aminopyridine-3-carboxamide. A pressure tube (Aldrich) was charged with 2-chloro-N-(4-methoxyphenyl)pyridine-3-carboxamide (139 mg, 0.524 mmol), 1-(4-pyridyl)piperidine-4-methylamine (100 mg, 0.524 mmol), triethylamine (0.22 mL), and ethanol (3 mL). The mixture was placed in a 110 C. bath for 5 days. The mixture was concentrated and the residue purified by RPHPLC, yielding 52 mg (24%) of the title compound as a hydrochloride salt. 1NMR, IR; IS-MS, m/e 418 (m+1); Analysis for C25H26N5O2.2HCl: Calcd: C, 58.78; H, 5.96; N, 14.28; Found: C, 58.74; H, 5.90; N, 13.91.

The synthetic route of 56149-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6610704; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 717843-56-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 717843-56-6, name is 3-Bromo-2-methoxy-5-methylpyridine, molecular formula is C7H8BrNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 172 (7bR,11aS)-N-(2-Methoxy-5-methyl-3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-6-amine A solution of tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4] oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)Carboxylate from Example 56, Part B (968 mg, 2.81 mmol), 3-bromo-2-methoxy-5-methylpyridine (515 mg, 2.55 mmol), and NaOt-Bu (404 mg, 4.20 mmol) in anhydrous toluene (40 mL) was stirred under an argon atmosphere in a sealable test tube. The mixture was degassed with argon at 85 C. for 30 min then cooled to 50 C. Tris(dibenzylideneacetone)dipalladium(0) (62 mg, 67 mumol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (84.0 mg, 135 mumol) were added; the reaction was sealed and heated at 85 C. for 16 h. The reaction was cooled to room temperature, diluted with EtOAc, filtered through a bilayer pad of diatomaceous earth and silica gel, and concentrated. Purification of the residue by flash column chromatography (silica gel, 10-50% EtOAc/hexanes) provided tert-butyl (7bR,11aS)-6-(2-methoxy-5-methyl-3-pyridinyl)amino-1,2,7b, 10,11,11 a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate (1.16 g, 89%). A solution of the intermediate in CH2Cl2 (20 mL) at -10 C. was treated with TFA (6 mL) and stirred for 1 h. Upon concentration in vacuo, the residue was partitioned between a 1:1 solution of CH2Cl2/satd NaHCO3 (100 mL). The aqueous phase was extracted with CH2Cl2 (4*75 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography [silica gel, 5-50% (80:18:2 CHCl3/MeOH/concd NH4OH)/CH2Cl2]and trituration with CH2Cl2/Et2O/hexanes provided the title compound of Example 172 (590 mg, 65%) as a tan solid: mp 122-124 C.; 1H NMR (300 MHz, CDCl3) delta 7.40 (s, 1H), 6.99 (s, 1H), 6.88 (s, 1H), 6.77 (s, 1H), 5.84 (br s, 1H), 4.75 (d, J=14.1 Hz, 1H), 4.58 (d, J=14.1 Hz, 1H), 4.3414.16 (m, 1H), 4.01 (s, 3H), 3.89-3.69 (m, 1H), 3.58-3.39 (m, 1H), 3.38-3.13 (m, 2H), 3.11-2.99 (m, 1H), 2.98-2.85 (m, 2H), 2.81-2.68 (m, 1H), 2.61-2.42 (m, 1H), 2.19 (s, 3H), 2.01-1.77 (m, 3H); ESI MS m/z 367 [C21H26N4O2+H]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 717843-56-6, 3-Bromo-2-methoxy-5-methylpyridine.

Reference:
Patent; Bristol-Myers Squibb Company; US6849619; (2005); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 86847-84-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide, molecular formula is C10H13ClN2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation 10 : N-(6-Chloro-3 propionamide; To a dry solution of N-(6-chloropyridin-2-yl)-2,2-dimethyl propionamide (Preparation 9, 8.0g, 37.6mmol) in THF (12OmL), cooled to -780C, was added dropwise, a solution of tert- butyllithium in pentane (1.7M, 48.7mL, 82.8mmol) over 40min. The reaction was stirred at -780C for 3h before adding a solution of iodine (11.46g, 45.1mmol) in THF (4OmL) dropwise. The mixture was EPO brought up to rt and stirred for 16h. 2M HCl (3OmL) was added to the reaction, and after 20min the solvent was removed in vacuo. Crude material was partitioned between EtOAc (20OmL) and water (15OmL). Organics were separated and washed with 10% sodium thiosulfate solution (4xl00mL) then NaHCO3 solution (2xl00mL), dried (MgSO4) and the solvent removed in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2) to give the title compound, m/z (ES+) = 338.93 [M+ H]+.

According to the analysis of related databases, 86847-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem